A practical synthesis of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane

The rigid piperazine homologue 2,5-diazabicyclo[2.2.1]heptane (DBH) finds extensive application in medicinal chemistry and pharmaceutical research, but access to this scaffold is non-trivial. This letter details a concise synthetic sequence that gives ready access to DBH on gram scale. The route fea...

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Bibliographic Details
Published in:Tetrahedron letters 2013-09, Vol.54 (39), p.5345-5347
Main Authors: Beinat, Corinne, Banister, Samuel D., McErlean, Christopher S.P., Kassiou, Michael
Format: Article
Language:English
Subjects:
2,5-Diazabicyclo[2.2.1]heptane
Amines
Heterocycles
Homology
Nicotinic acetylcholine receptors
Pharmaceuticals
Reduction
Scaffolds
Synthesis (chemistry)
Tetrahedrons
Transannular cyclisation
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Summary:The rigid piperazine homologue 2,5-diazabicyclo[2.2.1]heptane (DBH) finds extensive application in medicinal chemistry and pharmaceutical research, but access to this scaffold is non-trivial. This letter details a concise synthetic sequence that gives ready access to DBH on gram scale. The route features a Staudinger reduction of an azide to facilitate a transannular cyclisation
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.07.092